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CHEBI:3558 - cerivastatin

ChEBI IDCHEBI:3558
ChEBI Namecerivastatin
Stars
Definition(3R,5S)-3,5-dihydroxyhept-6-enoic acid in which the (7E)-hydrogen is substituted by a 4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl group. Formerly used (as its sodium salt) to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle toxicity.
Secondary ChEBI IDCHEBI:503465
Last Modified22 February 2017
DownloadsMolfile
FormulaC26H34FNO5
Net Charge0
Average Mass459.558
Monoisotopic Mass459.24210
SMILESCOCc1c(C(C)C)nc(C(C)C)c(/C=C/[C@@H](O)C[C@@H](O)CC(=O)O)c1-c1ccc(F)cc1
InChIInChI=1S/C26H34FNO5/c1-15(2)25-21(11-10-19(29)12-20(30)13-23(31)32)24(17-6-8-18(27)9-7-17)22(14-33-5)26(28-25)16(3)4/h6-11,15-16,19-20,29-30H,12-14H2,1-5H3,(H,31,32)/b11-10+/t19-,20-/m1/s1
InChIKeySEERZIQQUAZTOL-ANMDKAQQSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor  Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme.
Application:
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
ChEBI Ontology
Outgoing Relation(s)
cerivastatin (CHEBI:3558) is a dihydroxy monocarboxylic acid (CHEBI:35972)
cerivastatin (CHEBI:3558) is a pyridines (CHEBI:26421)
cerivastatin (CHEBI:3558) is a statin (synthetic) (CHEBI:87635)
cerivastatin (CHEBI:3558) is conjugate acid of cerivastatin(1−) (CHEBI:406059)
Incoming Relation(s)
cerivastatin(1−) (CHEBI:406059) is conjugate base of cerivastatin (CHEBI:3558)
IUPAC Name 
(3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-di(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
INN  Source
cerivastatinChemIDplus
Synonyms  Source
CerivastatinKEGG COMPOUND
(3R,5S,E)-7-(4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl)-3,5-dihydroxyhept-6-enoic acidChEMBL
(3R,5S,6E)-7-(4-(p-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridyl)-3,5-dihydroxy-6-heptenoic acidChemIDplus
(3R,5S,6E)-7-(4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl)-3,5-dihydroxy-6-heptenoic acidChemIDplus
cerivastatin acidChEBI
Manual XrefsDatabases
C07966KEGG COMPOUND
D07661KEGG DRUG
DB00439DrugBank
CerivastatinWikipedia
577DrugCentral
Registry NumbersSources
Beilstein:8366578Beilstein
CAS:145599-86-6KEGG COMPOUND
CAS:145599-86-6ChemIDplus
Citations